Acetic Acid → HCID 70937102, compound

HRID 1875259Notes

Reaction equation

HRID 1875259 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].CC(O)=O.[Cl:23][C:24]1[N:25]=[C:26]([S:46]([NH:49][CH3:50])(=[O:48])=[O:47])[N:27]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:28]=1[CH2:29][O:30][Si](C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:23][C:24]1[N:25]=[C:26]([S:46]([NH:49][CH3:50])(=[O:48])=[O:47])[N:27]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:43])[CH3:44])[C:28]=1[CH2:29][OH:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68721249HCID 68721249, compound

Product 1

HCID 70937102HCID 70937102, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of TBAF (1.2 mL, 1.2 mmol) was neutralized with a drop of HOAc and added to a solution of 4-chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-N-methyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonamide in THF (3 mL). The reaction mixture was stirred for 2 h at RT. Sat'd NaHCO3 was added and the aqueous phase was extracted with CH2Cl2. The combined organic phase was dried (Na2SO4), filtered, and evaporated to give 4-chloro-5-(hydroxymethyl)-N-methyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonamide as a light yellow oil that was used without purification and assumed to be quantitative.

Workup

  1. extractionthe aqueous phase was extracted with CH2Cl2
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-70ba431f8ae9458c9f62ea7a00f33b79
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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